title: Structure-activity relationships of larvicidal monoterpenes and derivatives against Aedes aegypti Linn.
abstract: In the search for larvicidal compounds against Aedes aegypti L. (Diptera: Culicidae), a collection of monoterpenes were selected and evaluated. R- and S-limonene exhibited the highest larvicidal potency (LC(50)=27 and 30 ppm, respectively), followed by γ-terpinene (LC(50)=56 ppm) and RS-carvone (LC(50)=118 ppm). Structural characteristics which may contribute to the understanding of the larvicidal activity of monoterpenes were empirically identified. The presence of heteroatoms in the basic hydrocarbon structure decreases larvicidal potency. Conjugated and exo double bonds appear to increase larvicidal potency. Replacement of double bonds by more reactive epoxides decreases the larvicidal potency. The presence of hydroxyls in the cyclic structure resulted in decreased potency, probably due to increased polarity indicanting that lipophilicity seems to play an important role in increasing the larvicidal potency in this set of compounds.
authors.affiliation: Medicinal Chemistry Laboratory, Pharmacy Department, Federal University of Sergipe, Av. Marechal Rondon S/N, Rosa Elze, São Cristóvão, Sergipe, Brazil.
authors.forename: Sandra R L
authors.initials: SR
authors.lastname: Santos
authors.forename: Manuela A
authors.initials: MA
authors.lastname: Melo
authors.forename: Andrea Valença
authors.initials: AV
authors.lastname: Cardoso
authors.forename: Roseli L C
authors.initials: RL
authors.lastname: Santos
authors.forename: Damião P
authors.initials: DP
authors.lastname: de Sousa
authors.forename: Sócrates C H
authors.initials: SC
authors.lastname: Cavalcanti
mesh_terms: D000330:Aedes / Q000187:drug effects*; D000818:Animals; D053138:Cyclohexenes / Q000633:toxicity; D007306:Insecticides / Q000737:chemistry / Q000633:toxicity*; D007814:Larva / Q000187:drug effects; D000077222:Limonene; D039821:Monoterpenes / Q000737:chemistry / Q000633:toxicity*; D013329:Structure-Activity Relationship; D013729:Terpenes / Q000633:toxicity
chemical_list: D053138:Cyclohexenes; D007306:Insecticides; D039821:Monoterpenes; D013729:Terpenes; D000077222:Limonene